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ANISOLE                                     181


Anisole (Methyl phenate, Phenyl methyl ether), CGH5.O.CH3
Cahours, A?malen^ 1851, 78, 226.

5 grms.   sodium.

100 c.c.       methyl alcohol,

20 grms.   phenol.

40           methyl iodide.

The methyl alcohol is poured into a round flask (250 c.c.)
connected with an upright condenser. The sodium, cut into
small pieces, is then added, the flask being detached from the
condenser for 'a moment and replaced. When the sodium has
dissolved, the phenol and methyl iodide are added. The mixture
is heated on the water-bath until the solution has no longer an
alkaline reaction (two to three hours). As much as possible of
the methyl alcohol is distilled off on the water-bath and water
added to the amber-coloured residue. A colourless oil separates
out, which is extracted with ether. The ethereal solution is
dehydrated over calcium chloride and distilled, first on the
water-bath until the ether has been driven off, and then over
the flame. Almost the whole of the residue distils at 150  155.
Yield, nearly theoretical.

Properties.  Colourless liquid, possessing an agreeable smell ;
b. p. 154 ; sp. gr. o'99i at 15. See Appendix, p. 294.
Hexahydrophenol (Cyclohexanol), C0H11.OH
Sabatier and Senderens, Compt. rend.) 1901, 132, 210.
50 grms. phenol.
The phenol is reduced with hydrogen in presence of finely
divided metallic nickel ; which acts as a catalyst. The
apparatus is shown in Fig. 79.